18-Crown-6 → 3-Acetoxymethyl-5-[bromomethyl]benzoic acid, ethyl ester

HRID 1531926Notes

Reaction equation

HRID 1531926 reaction equation
C1OCCOCCOCCOCCOCCOC1.[C:19]([O-:22])(=[O:21])[CH3:20].[K+].[CH2:24]([O:26][C:27](=[O:38])[C:28]1[CH:33]=[C:32]([CH2:34][Br:35])[CH:31]=[C:30]([CH2:36]Br)[CH:29]=1)[CH3:25]>C(#N)C>[C:19]([O:22][CH2:36][C:30]1[CH:29]=[C:28]([CH:33]=[C:32]([CH2:34][Br:35])[CH:31]=1)[C:27]([O:26][CH2:24][CH3:25])=[O:38])(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 2855718-Crown-6HCID 517044Potassium AcetateHCID 154403433,5-Bis(bromomethyl)benzoic acid ethyl ester

Product 1

HCID 1317224333-Acetoxymethyl-5-[bromomethyl]benzoic acid, ethyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 18-crown-6 (0.103 g) in acetonitrile (15 ml) was added potassium acetate (0.38 g). After 30 minutes 3,5-bis[bromomethyl]benzoic acid ethyl ester (2.61 g) was added and the mixture was stirred overnight. The mixture was partitioned between ethyl acetate and water. The organic phase was dried (MgSO4) and evaporated and the residue purified by chromatography eluting with 10% ethyl acetate in isohexane. Yield 0.97 g.

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. dry with materialThe organic phase was dried (MgSO4)
  3. customevaporated
  4. customthe residue purified by chromatography
  5. washeluting with 10% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-a7967876968d44fd96385f5cc263c81e
Source dataset
uspto-grants-2001_03
Patent number
US06200981B1

Reaction notes

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